5-(3-chlorophenyl)-1,3,4-oxadiazol-2(3H)-one | 85929-41-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-(3-chlorophenyl)-1,3,4-oxadiazol-2(3H)-one
• 英文别名: 5-(3-chlorophenyl)-3H-1,3,4-oxadiazol-2-one
• CAS: 85929-41-5
• 化学式: C₈H₅ClN₂O₂
• 分子量: 196.593
• InChiKey: FXHVMBKWFKRQHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(3-chlorophenyl)-1,3,4-oxadiazol-2(3H)-one 在 氯化亚砜 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and Biological Activity ofO,O-DialkylS-(5-Aryl-l,3,4-oxadiazol-2(3H)-on-3-yl)methyl Phosphorothioates and Phosphorodithioates

  摘要：

  合成了一些恶二唑磷衍生物，寻找杀虫先导化合物。 1,3,4-恶二唑-2-酮通过N-羟甲基衍生物转化为相应的N-氯甲基衍生物。由这些衍生物制备了多种O,O-二甲基二硫代磷酸酯4、O,O-二甲基硫代磷酸酯5和O,O-二异丙基硫代磷酸酯6。检查了这些磷衍生物对家蝇的杀虫活性和抗昆虫活性。使用家蝇头作为酶源来检测乙酰胆碱酯酶（抗 AChE）活性。大多数化合物 4 和 5 的接触毒性与类似的甲硫磷杀虫剂一样高，这似乎与强抗乙酰胆碱酯酶活性相关。另一方面，所有化合物6都表现出较高的AChE抑制活性，但杀虫活性较差。

  DOI：

  10.1080/00021369.1983.10865735
• 作为产物：
  描述：

  1,1-Dimethylethyl 2-[(3-chlorophenyl)methylene]hydrazinecarboxylate 在 N-氯代丁二酰亚胺 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.18h， 生成 5-(3-chlorophenyl)-1,3,4-oxadiazol-2(3H)-one
  参考文献：
  名称：

  Synthesis of 5-aryl-3H-[1,3,4]oxadiazol-2-ones from N′-(chloro-aryl-methylene)-tert-butylcarbazates using basic alumina as an efficient and recyclable surface under solvent-free condition

  摘要：

  The synthesis of biologically important 5-aryl-3H-[1,3,4]oxadiazol-2-ones has been carried out by heating the easily synthesized N'-(chloro-aryl-methylene)-tert-butylcarbazates on basic alumina surface under solvent-free condition. The dual characteristic of basic alumina as a solid support as well as a nucleophile is successfully exploited in these reactions. The method provides special attributions such as reduced reaction times, easier work-up procedures, and good to excellent yields as well as increased purity of products and most importantly environmentally friendly protocols. The basic alumina is easily recovered and utilized for further reactions several times without serious loss of activity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.11.128

文献信息

• [EN] COMPOUNDS<br/>[FR] COMPOSÉS
  申请人：UCL BUSINESS LTD

  公开号：WO2020043866A1

  公开（公告）日：2020-03-05

  A compound for use in the treatment of a disease ameliorated by the inhibition of Notum of formula (I): (I)

  一种用于治疗通过抑制公式（I）中的Notum改善的疾病的化合物：（I）
• 5-Phenyl-1,3,4-oxadiazol-2(3<i>H</i>)-ones Are Potent Inhibitors of Notum Carboxylesterase Activity Identified by the Optimization of a Crystallographic Fragment Screening Hit
  作者：William Mahy、Nicky J. Willis、Yuguang Zhao、Hannah L. Woodward、Fredrik Svensson、James Sipthorp、Luca Vecchia、Reinis R. Ruza、James Hillier、Svend Kjær、Sarah Frew、Amy Monaghan、Magda Bictash、Patricia C. Salinas、Paul Whiting、Jean-Paul Vincent、E. Yvonne Jones、Paul V. Fish

  DOI：10.1021/acs.jmedchem.0c01391

  日期：2020.11.12

  Carboxylesterase Notum is a negative regulator of the Wnt signaling pathway. There is an emerging understanding of the role Notum plays in disease, supporting the need to discover new small-molecule inhibitors. A crystallographic X-ray fragment screen was performed, which identified fragment hit 1,2,3-triazole 7 as an attractive starting point for a structure-based drug design hit-to-lead program. Optimization of 7 identified oxadiazol-2-one 23dd as a preferred example with properties consistent with druglike chemical space. Screening 23dd in a cell-based TCF/LEF reporter gene assay restored the activation of Wnt signaling in the presence of Notum. Mouse pharmacokinetic studies with oral administration of 23dd demonstrated good plasma exposure and partial blood-brain barrier penetration. Significant progress was made in developing fragment hit 7 into lead 23dd (>600-fold increase in activity), making it suitable as a new chemical tool for exploring the role of Notum-mediated regulation of Wnt signaling.
• Some 1-aroyl-4,4-dialkylsemicarbazides and their cyclization to afford 5-aryl-1,3,4-oxadiazol-2(3H)-ones
  作者：John S. Davidson

  DOI：10.1007/bf00810111

  日期：——
• KAMIZONO, HIROSHI;ETO, MORIFUSA, AGR. AND BIOL. CHEM., 1983, 47, N 4, 701-706
  作者：KAMIZONO, HIROSHI、ETO, MORIFUSA

  DOI：——

  日期：——
• DAVIDSON, JOHN S., MONTASH. CHEM., 119,(1988) N 8-9, C. 1027-1029
  作者：DAVIDSON, JOHN S.

  DOI：——

  日期：——